WO2012002094A1 - Modificateur d'orientation pour pigment de surbrillance - Google Patents

Modificateur d'orientation pour pigment de surbrillance Download PDF

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Publication number
WO2012002094A1
WO2012002094A1 PCT/JP2011/062589 JP2011062589W WO2012002094A1 WO 2012002094 A1 WO2012002094 A1 WO 2012002094A1 JP 2011062589 W JP2011062589 W JP 2011062589W WO 2012002094 A1 WO2012002094 A1 WO 2012002094A1
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WO
WIPO (PCT)
Prior art keywords
pigment
orientation
paint
bright
olefin
Prior art date
Application number
PCT/JP2011/062589
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English (en)
Japanese (ja)
Inventor
司 芥川
雅弘 高木
大輔 三冨
貴則 松山
Original Assignee
共栄社化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 共栄社化学株式会社 filed Critical 共栄社化学株式会社
Priority to US13/806,963 priority Critical patent/US20130102717A1/en
Priority to JP2012522530A priority patent/JP5256379B2/ja
Priority to CN2011800319100A priority patent/CN102959025A/zh
Publication of WO2012002094A1 publication Critical patent/WO2012002094A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/29—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for multicolour effects
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/36—Pearl essence, e.g. coatings containing platelet-like pigments for pearl lustre
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/45—Anti-settling agents

Definitions

  • the present invention is used to form an orientation coating film having a different color tone depending on the direction in which an automobile body exterior, a home appliance housing, or a plastic product is coated with a glitter pigment-containing paint and viewed.
  • the present invention relates to an orientation improver that improves the orientation of a pigment.
  • Car body exteriors, home appliance housings such as mobile phones, and plastic products for daily necessities are painted in a metallic style with excellent design and glittering decorativeness that match the fashion and consumer aesthetics. Often done.
  • an aluminum flake pigment having an orientation called so-called flip-flop property that shows different colors depending on whether the coated surface is viewed from the front direction or the oblique direction is used. Bright pigment-containing paints are widely used.
  • Patent Document 1 discloses that a copolymer of a wax or resin, an ⁇ -olefin and maleic anhydride is monovalent such as an aliphatic alcohol or aromatic alcohol having 6 to 60 carbon atoms.
  • An ink composition comprising a pigment dispersant composed of an ester-modified copolymer having a saponification value of 100 KOH ⁇ mg / g or less by esterification with alcohol and a pigment is disclosed.
  • Patent Document 2 discloses a method for producing a resin in which a copolymer of an ⁇ -olefin having 6 or more carbon atoms and maleic anhydride is reacted with one or more selected from oxyacids, amino acids and nonionic emulsifiers.
  • Patent Document 3 discloses a glittering paint composition containing a vehicle, a glittering pigment, and an acidic pigment dispersant having a total acid amount of 500 to 1500 ⁇ mol / g.
  • the painted surface is clearly reflected as a bright white highlight with a strong gloss when viewed from the front, and the painted surface is viewed from an oblique direction.
  • a versatile orientation improver that further improves the flip-flop property of the pigment while sufficiently dispersing the bright pigment so that it will appear dull and unsharp as a dark black shade with reduced gloss And luster pigment-containing coatings containing the same are desired.
  • the present invention has been made to solve the above-mentioned problems, and the coating film formed by applying the paint while sufficiently dispersing the bright pigment added to the bright pigment-containing paint is a flip-flop property of the bright pigment. It is an object of the present invention to provide an inexpensive orientation improver that can be further improved, is versatile, and can be easily produced, and an orientation paint containing the orientation improver and a bright pigment.
  • the bright pigment orientation improver according to claim 1, which has been made to achieve the above object, is a linear or branched ⁇ -olefin having at least 6 carbon atoms and anhydrous maleic acid.
  • R 1 is a linear or branched alkyl group having 6 to 30 carbon atoms, and n is a number of 5 to 60.
  • an ester compound having an acid value of 15 to 60 mg ⁇ KOH / g which is esterified with a polyethylene glycol monoalkyl ether having a hydrophilic / lipophilic balance of 9 to 19 To do.
  • the bright pigment-containing orientation coating composition according to claim 2 comprises 0.01 to 5% by weight of the ester compound of the glitter pigment according to claim 1 as a weight ratio in the coating composition. 1 to 50% by weight of the luster pigment dispersed by 10% and 10 to 95% by weight of the vehicle.
  • the bright pigment-containing orientation paint according to claim 3 is the paint according to claim 2, wherein the bright pigment is an aluminum flake pigment, a titanium flake pigment, a stainless flake pigment, a colored aluminum pigment, or a metal oxide-coated mica pigment.
  • the oriented cured coating film according to claim 4 is formed by coating the bright pigment-containing oriented paint according to any one of claims 2 to 3 on a substrate and curing it. It is characterized by.
  • the bright pigment orientation improver of the present invention can be added to a bright pigment-containing paint to sufficiently disperse the bright pigment, has versatility, and can be easily manufactured in a short process. It is.
  • the coating film formed by applying and curing the bright pigment-containing oriented paint of the present invention containing the orientation improver and the bright pigment on the substrate is more bright than the conventional dispersant-containing oriented paint.
  • the flip-flop property of the pigment is further improved. For this reason, this coating film clearly appears as a bright white highlight with a strong glossiness in the front direction, and appears dull as a dark black shade with a reduced luster in the diagonal direction. Therefore, it is rich in design.
  • the coating film is hard and excellent in weather resistance and heat resistance as well as scratch resistance.
  • the orientation improver of the present invention is an ⁇ -olefin-maleic anhydride obtained by copolymerizing a linear or branched ⁇ -olefin and maleic anhydride such as 1-dodecene or 1-tetradecene and having 6 or more carbon atoms.
  • R 1 — (OCH 2 CH 2 ) n —OH (wherein R 1 is a linear or branched alkyl group having 6 to 30 carbon atoms, n is 5 to 60). It comprises an ester compound in which the terminal hydroxyl group of the polyethylene glycol monoalkyl ether represented by 60) undergoes ring-opening addition reaction.
  • the ester compound preferably has an acid value of 15 to 60 mg ⁇ KOH / g by controlling the reaction temperature to 100 ° C. to 250 ° C. and the reaction time to 1 hour to 8 hours, respectively.
  • the ester compound may be a single compound or a mixture of plural compounds.
  • This orientation improver exhibits an excellent dispersibility of the bright pigment and an excellent orientation of the bright pigment, that is, a flip-flop property, due to the ester compound.
  • This orientation improver greatly improves the dispersibility and orientation of the bright pigment compared to conventional acidic dispersants.
  • the mechanism of action is not necessarily clear, but is as follows.
  • the ⁇ -olefin-maleic anhydride copolymer in this ester compound is obtained by sequentially converting the terminal unsaturated group of the ⁇ -olefin and the unsaturated group of maleic anhydride, which is difficult to homopolymerize, through a charge transfer complex reaction.
  • alternating copolymerization an alternating copolymer having a linear copolymer main chain is obtained.
  • An ester compound of an ⁇ -olefin-maleic anhydride copolymer and a polyethylene glycol monoalkyl ether which is such an alternating copolymer, has a hydrophobic site such as a hydrocarbon group derived from ⁇ -olefins and an anhydride.
  • the arrangement with a hydrophilic site such as a carboxyl group formed by ring-opening addition of maleic anhydride groups derived from maleic acids is controlled and alternately arranged.
  • This ester compound has a good adsorption efficiency of the bright pigment to the interface of its copolymer main chain due to the regular alternating copolymer structure of ⁇ -olefin-maleic anhydride copolymer. Compared to a random copolymer such as a copolymer with an acrylic compound, it is presumed that the effect of dispersing the bright pigment is much higher.
  • this ester compound has a relatively hydrophobic terminal alkyl group derived from polyethylene glycol monoalkyl ethers branched from a hydrophobic copolymer main chain via a relatively hydrophilic polyethylene glycol group. While dissimilar in nature, the hydrophobic hydrocarbon group derived from ⁇ -olefins has a different property in that it is directly bonded while branched from the hydrophobic copolymer main chain. It has a branched structure.
  • both hydrophobic groups of terminal alkyl groups derived from polyethylene glycol monoalkyl ethers far from the copolymer main chain and hydrocarbon groups derived from ⁇ -olefins close to the copolymer main chain are adsorbed on the bright pigment. Since it acts as a site, it is presumed that the steric hindrance effect is increased and the orientation of the glitter pigment, that is, the flip-flop property, is much improved as compared with the polyester polyester body having no hydrophobic group.
  • the ⁇ -olefin constituting the ester compound is not particularly limited as long as it is a linear or branched unsaturated hydrocarbon having 6 or more carbon atoms, but may be an unsaturated hydrocarbon having 6 to 30 carbon atoms.
  • Preferable examples include 1-dodecene, 1-tetradecene, and mixtures thereof.
  • maleic anhydrides constituting this ester compound include unsubstituted maleic anhydride and bromomaleic anhydride.
  • n is less than 5
  • the terminal alkyl group derived from polyethylene glycol monoalkyl ethers is too close to the copolymer main chain, and if its n exceeds 60, the terminal alkyl group is removed from the copolymer main chain. In any case, the effect on the luster pigment interface becomes small, and sufficient dispersibility and orientation cannot be expressed.
  • Polyethylene glycol monoalkyl ethers preferably have a hydrophilic / lipophilic balance (HLB) of, for example, an HLB of 9 to 19 by the Griffin method.
  • HLB hydrophilic / lipophilic balance
  • the orientation improver may consist only of this ester compound, but may contain a medium if necessary.
  • the glittering pigment-containing orientation paint of the present invention has a flip-flop property by dispersing its ester compound, which is an orientation improver of the glitter pigment, in a weight ratio of 0.01 to 5% by weight in the paint. It contains a paint component of 1 to 50% by weight of the bright pigment and 10 to 95% by weight of the vehicle, and optionally a paint component of an additive.
  • the content of the glitter pigment is less than 1% by weight, it is difficult to exhibit the glitter, while when it exceeds 50% by weight, the appearance of the coating film is deteriorated. 5-30% is even more preferable.
  • the bright pigment is a flaky flake pigment having an average particle diameter of about several tens of ⁇ m, specifically about 10 to 30 ⁇ m, for example, a metal flake pigment such as a flaky aluminum flake pigment, titanium flake pigment or stainless steel flake pigment.
  • a colored aluminum pigment coated with an organic or inorganic colored pigment a metal oxide in which the surface of a mica pigment having a low refractive index is coated with a metal oxide having a high refractive index such as titanium oxide, iron oxide, silica, alumina, or zirconia Coated mica pigment; metal oxide-coated silica flake pigment coated on silica flake surface with metal oxide as described above; metal oxide-coated alumina flake pigment coated on alumina flake surface with metal oxide as described above; Metal oxide-coated glass flake pigment with glass flake surface coated with such metal oxide; Examples thereof include iron oxide pigments; cholesteric liquid crystal polymers.
  • the vehicle contained in the glittering pigment-containing alignment paint disperses the glittering pigment, and is composed of a resin for forming a coating film and, if necessary, a crosslinking agent or a solvent.
  • a resin for forming a coating film constituting the vehicle include acrylic resins, polyester resins, alkyd resins, fluororesins, epoxy resins, polyurethane resins, polyether resins and the like. In particular, acrylic resins and polyester resins are preferably used. .
  • These coating film forming resins may be used alone or in combination of two or more.
  • the coating film forming resin includes a curable type resin and a curable lacquer type resin that does not have a curable type. Usually, a curable type resin is used.
  • a curable resin When a curable resin is used, it is used by mixing with a crosslinking agent such as an amino resin, a (block) polyisocyanate compound, an amine, a polyamide, or a polyvalent carboxylic acid, and the curing reaction proceeds at heating or normal temperature To form a paint film.
  • a crosslinking agent such as an amino resin, a (block) polyisocyanate compound, an amine, a polyamide, or a polyvalent carboxylic acid
  • a resin for forming a coating film having no curability may be used in combination with a type having curability.
  • An additive such as a colored pigment may be added to the glittering pigment-containing alignment paint in an addition amount within a range that does not interfere with the expression of the flip-flop property of the glittering pigment.
  • colored pigments examples include organic pigments such as azo lake pigments, phthalocyanine pigments, indigo pigments, perylene pigments, quinophthalone pigments, dioxazine pigments, quinacridone pigments, isoindolinone pigments, and metal complex pigments.
  • organic pigments such as azo lake pigments, phthalocyanine pigments, indigo pigments, perylene pigments, quinophthalone pigments, dioxazine pigments, quinacridone pigments, isoindolinone pigments, and metal complex pigments.
  • inorganic pigments such as yellow iron oxide, red iron oxide, titanium dioxide, and carbon black.
  • Anti-precipitation agents such as polyamide wax, which is a lubricating dispersion of aliphatic amides, and polyethylene wax, which is a colloidal dispersion mainly composed of polyethylene oxide, in addition to the above-mentioned components, and a bright pigment-containing orientation coating; curing catalyst; ultraviolet rays Absorbers; antioxidants; leveling agents; surface conditioners such as silicon and organic polymers; anti-sagging agents; thickeners; antifoaming agents; lubricants; additives such as crosslinkable polymer particles that are microgels These may be added as necessary. These additives can improve the performance of paints and coating films by blending in an amount of 15 parts by mass or less with respect to 100 parts by mass of the vehicle (based on solid content).
  • the orientation improver can be contained in these paints regardless of non-aqueous or water-based glitter pigment-containing orientation paints.
  • the orientation improver may be used as a salt or as a neutralized product thereof.
  • the solvent is not particularly limited as long as it dissolves or disperses the vehicle, and for example, an organic solvent and / or water can be used.
  • the organic solvent include solvents usually used in paints, and more specifically, hydrocarbons such as toluene and xylene; ketones such as acetone and methyl ethyl ketone; esters such as ethyl acetate, cellosolve acetate and butyl cellosolve; alcohol Examples are shown.
  • an organic solvent is regulated from the viewpoint of environmental protection, it is preferable to use water.
  • an appropriate amount of a hydrophilic organic solvent may be contained.
  • the oriented cured coating film of the present invention has a thickness of 5 to 50 ⁇ m because the glittering pigment-containing oriented paint is coated and cured by coating, spraying and brushing on the substrate to be coated. Is formed.
  • a metal plate or plastic plate made of any material or shape such as an automobile body exterior, a household appliance housing such as a mobile phone, various cases, or a plastic product is used.
  • This orientation-cured coating film is used for metallic substrates that are required to have high design and glittering decorativeness that are tailored to the fashion and consumer's aesthetics, especially for automobile body exteriors and mobile phone housings. It is for finishing.
  • the oriented cured coating film has no unevenness because the bright pigments contained in it are uniformly dispersed, and the bright pigments show no difference when viewed from the front or oblique direction. It is beautiful because it has flip-flops that show different colors.
  • the orientation improving agent for the bright pigment of the present invention and the bright pigment-containing orientation paint containing the same were prepared to produce an orientation cured coating film.
  • Example 1 In a flask equipped with a reflux condenser, a thermometer, a stirrer, and a dropping tank, 45.9 g of dialen 124 (manufactured by Mitsubishi Chemical Corporation: dialen is a registered trademark) which is a 1-dodecene / 1-tetradecene mixture as an ⁇ -olefin. And 28.66 g of maleic anhydride and 35.9 g of xylene were charged, replaced with nitrogen gas, and then heated to 130 ° C. with stirring. While stirring there, a mixture of 1.2 g of perbutyl O (manufactured by NOF Corporation: trade name) and 21.36 g of xylene was dropped over 2 hours.
  • dialen 124 manufactured by Mitsubishi Chemical Corporation: dialen is a registered trademark
  • maleic anhydride and 35.9 g of xylene were charged, replaced with nitrogen gas, and then heated to 130 ° C. with stirring. While stirring there, a mixture of 1.2
  • BLAUNON SR-715 (Aoki Yushi Kogyo Co., Ltd., trade name) which is an adduct of stearyl polyoxyethylene 15 mol as polyethylene glycol monoalkyl ethers was added.
  • the mixture was reacted at about 160 ° C. for about 2 hours with stirring to synthesize a modified product which was an ester compound of an ⁇ -olefin-maleic anhydride copolymer and a polyethylene glycol monoalkyl ether. Its acid value was 32 mg ⁇ KOH / g.
  • the reaction mixture of this modified product was cooled to 100 ° C. or lower and then diluted to 50% with 3-methyl-3-methoxybutanol to obtain a bright pigment orientation improver.
  • Example 2 In a flask equipped with a reflux condenser, a thermometer, a stirrer, and a dropping tank, 45.9 g of diallene 124 (manufactured by Mitsubishi Chemical Corporation) as an ⁇ -olefin, 28.66 g of maleic anhydride, and 35. of toluene. 9 g was charged and replaced with nitrogen gas, and then heated to 110 ° C. with stirring. While stirring there, a mixture of 0.5 g of perbutyl L (manufactured by NOF Corporation: trade name) and 21.36 g of toluene was dropped over 2 hours.
  • diallene 124 manufactured by Mitsubishi Chemical Corporation
  • BLAUNON SR-707 (trade name, manufactured by Aoki Yushi Kogyo Co., Ltd.), which is an adduct of 7 mol of stearyl polyoxyethylene, was added as polyethylene glycol monoalkyl ethers.
  • the mixture was reacted at about 160 ° C. for about 2 hours with stirring to synthesize a modified product which was an ester compound of an ⁇ -olefin-maleic anhydride copolymer and a polyethylene glycol monoalkyl ether. Its acid value was 55 mg ⁇ KOH / g.
  • the reaction mixture of this modified product was cooled to 100 ° C. or lower and then diluted to 50% with isopropyl alcohol to obtain a bright pigment orientation improver.
  • Example 3 In a flask equipped with a reflux condenser, a thermometer, a stirrer, and a dropping tank, 30 g of linearene 18 (produced by Idemitsu Kosan Co., Ltd .: trade name), which is 1-octadecene as an ⁇ -olefin, and 28.66 g of maleic anhydride, After charging 35.9 g of xylene and replacing with nitrogen gas, it was heated to 130 ° C. with stirring.
  • linearene 18 produced by Idemitsu Kosan Co., Ltd .: trade name
  • a solution containing an ⁇ -olefin-maleic anhydride copolymer having a weight average molecular weight of 7000 in terms of polystyrene was obtained.
  • 256.6 g of BLAUNON EL-1530 (Aoki Yushi Kogyo Co., Ltd., trade name), which is an adduct of 30 mol of lauryl polyoxyethylene, was added as polyethylene glycol monoalkyl ethers.
  • the reaction product was stirred at about 160 ° C. for about 2 hours to synthesize a modified product which was an ester compound of an ⁇ -olefin-maleic anhydride copolymer and a polyethylene glycol monoalkyl ether. Its acid value was 20 mg ⁇ KOH / g.
  • the reaction mixture of this modified product was cooled to 100 ° C. or lower and then diluted to 50% with isopropyl alcohol to obtain a bright pigment orientation improver.
  • Newpol 50HB-100 manufactured by Sanyo Kasei Kogyo Co., Ltd .: trade name
  • polyoxyethylene polyoxypropylene butyl ether was added, and then at about 160 ° C. for about 2 hours.
  • the mixture was reacted with stirring to obtain a modified product which was an ester compound of an ⁇ -olefin-maleic anhydride copolymer and polyoxyethylene polyoxypropylene butyl ether. Its acid value was 50 mg ⁇ KOH / g.
  • the reaction mixture of the modified product was cooled to 100 ° C. or lower and diluted to 50% with 3-methyl-3-methoxybutanol to obtain a dispersant.
  • the ⁇ -olefin-maleic anhydride copolymer obtained by copolymerizing an ⁇ -olefin having 6 or more carbon atoms and maleic anhydride as in Examples 1 to 3 has a hydroxyl group at the terminal.
  • a coating film obtained from a bright pigment-containing oriented paint prepared using an ester compound obtained by esterifying a polyoxyethylene alkyl ether as a bright pigment orientation improver has an F / F value indicating the degree of flip-flop properties. That is, the difference between the L * value at 15 ° and the L * value at 110 ° was large, indicating excellent flip-flop properties, that is, excellent orientation of the bright pigment.
  • the coating film obtained from the paints prepared using the dispersants of Comparative Examples 1 and 2 corresponding to the existing acidic dispersants is more F / than the one using the orientation improver of Examples 1 to 3.
  • the F value was much smaller and did not show much flip-flop properties.
  • the orientation improving agent for bright pigments of the present invention is used by adding to a bright pigment-containing paint for coating the exterior of metallic or plastic automobile bodies, housings, cases and the like. Since the oriented cured coating film obtained from this paint has a different color tone depending on the viewing direction, it is useful to clean the exterior.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

Selon l'invention, un modificateur d'orientation de faible coût est ajouté à de la peinture contenant un pigment de surbrillance pour disperser de manière adéquate le pigment de surbrillance, il permet à un film de peinture formé par application de peinture d'améliorer l'effet flip-flop du pigment de surbrillance, il est polyvalent et peut être facilement fabriqué. Le modificateur d'orientation pour pigment de surbrillance est obtenu par estérification d'un copolymère d'anhydride α-oléfine/maléique formé par copolymérisation d'une α-oléfine linéaire ou ramifiée avec au moins 6 atomes de carbone et un anhydride maléique; et d'un éther de monoalkyle de polyéthylèneglycol représenté par R1-(OCH2CH2)n-OH (formule dans laquelle, R1 est un groupe alkyle linéaire ou ramifié avec 6 à 30 atomes de carbone, et n est un nombre compris entre 5 et 60), et présentant un équilibre hydrophile-lipophile compris entre 9 et 19. Le modificateur d'orientation contient un composé d'ester possédant une valeur acide comprise entre 15 et 60 mg⋅KOH/g.
PCT/JP2011/062589 2010-06-28 2011-06-01 Modificateur d'orientation pour pigment de surbrillance WO2012002094A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US13/806,963 US20130102717A1 (en) 2010-06-28 2011-06-01 Orientation modifier for brightening pigment
JP2012522530A JP5256379B2 (ja) 2010-06-28 2011-06-01 光輝顔料の配向性改良剤
CN2011800319100A CN102959025A (zh) 2010-06-28 2011-06-01 闪光颜料的取向性改良剂

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010-145828 2010-06-28
JP2010145828 2010-06-28

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WO2012002094A1 true WO2012002094A1 (fr) 2012-01-05

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US (1) US20130102717A1 (fr)
JP (1) JP5256379B2 (fr)
CN (1) CN102959025A (fr)
WO (1) WO2012002094A1 (fr)

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* Cited by examiner, † Cited by third party
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WO2015147081A1 (fr) * 2014-03-26 2015-10-01 日本ペイント・オートモーティブコーティングス株式会社 Composition de revêtement aqueuse et procédé de formation d'un film de revêtement multicouche
WO2015147080A1 (fr) * 2014-03-26 2015-10-01 日本ペイント・オートモーティブコーティングス株式会社 Composition aqueuse de revêtement et procédé de formation de film multicouche appliqué en revêtement
JP2016107375A (ja) * 2014-12-05 2016-06-20 株式会社マキタ 電動工具及び動力工具
KR20160129288A (ko) * 2015-04-30 2016-11-09 한국화학연구원 신규한 수용성 공중합체 및 이의 제조방법
JP2019014790A (ja) * 2017-07-05 2019-01-31 株式会社Kri 撥水撥油性膜形成用塗布組成物及び撥水撥油性膜

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US9205304B1 (en) * 2014-10-17 2015-12-08 Acushnet Company Multi-coating layer color golf ball

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01261474A (ja) * 1988-04-13 1989-10-18 Toyo Ink Mfg Co Ltd 顔料分散剤およびそれを配合した感熱転写インキ組成物
JPH0489809A (ja) * 1990-08-03 1992-03-24 Toyo Ink Mfg Co Ltd 樹脂の製造方法，水性樹脂組成物の製造方法および樹脂組成物の製造方法
JPH09165489A (ja) * 1995-12-15 1997-06-24 Nippon Paint Co Ltd 水分散性樹脂組成物およびその製造方法
JP2005240013A (ja) * 2004-01-30 2005-09-08 Asahi Kasei Chemicals Corp 配向性に優れた自動車用メタリック塗料組成物
WO2006009219A1 (fr) * 2004-07-22 2006-01-26 Kansai Paint Co., Ltd. Composition de revêtement thermodurcissable à base d'eau et procédé de formation d'un film de revêtement
WO2009119143A1 (fr) * 2008-03-28 2009-10-01 東洋アルミニウム株式会社 Composition de pigment à base d'aluminium pour des matières aqueuses de revêtement et matières aqueuses de revêtement

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6335664A (ja) * 1986-07-31 1988-02-16 Nippon Oil & Fats Co Ltd 水系塗料組成物
JPH064777B2 (ja) * 1987-04-03 1994-01-19 大日精化工業株式会社 顔料組成物
IL94647A0 (en) * 1989-07-06 1991-04-15 Warner Lambert Co Polymer base blend compositions containing destructurized starch
JPH0489872A (ja) * 1990-08-03 1992-03-24 Toyo Ink Mfg Co Ltd 光硬化性被覆剤
US5573702A (en) * 1993-11-22 1996-11-12 Colgate-Palmolive Co. Liquid cleaning compositions with grease release agent
US6433039B1 (en) * 1996-05-20 2002-08-13 Xerox Corporation Ink jet printing with inks containing comb polymer dispersants
JP2962681B2 (ja) * 1996-06-12 1999-10-12 日華化学株式会社 耐久柔軟仕上剤

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01261474A (ja) * 1988-04-13 1989-10-18 Toyo Ink Mfg Co Ltd 顔料分散剤およびそれを配合した感熱転写インキ組成物
JPH0489809A (ja) * 1990-08-03 1992-03-24 Toyo Ink Mfg Co Ltd 樹脂の製造方法，水性樹脂組成物の製造方法および樹脂組成物の製造方法
JPH09165489A (ja) * 1995-12-15 1997-06-24 Nippon Paint Co Ltd 水分散性樹脂組成物およびその製造方法
JP2005240013A (ja) * 2004-01-30 2005-09-08 Asahi Kasei Chemicals Corp 配向性に優れた自動車用メタリック塗料組成物
WO2006009219A1 (fr) * 2004-07-22 2006-01-26 Kansai Paint Co., Ltd. Composition de revêtement thermodurcissable à base d'eau et procédé de formation d'un film de revêtement
WO2009119143A1 (fr) * 2008-03-28 2009-10-01 東洋アルミニウム株式会社 Composition de pigment à base d'aluminium pour des matières aqueuses de revêtement et matières aqueuses de revêtement

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015147081A1 (fr) * 2014-03-26 2015-10-01 日本ペイント・オートモーティブコーティングス株式会社 Composition de revêtement aqueuse et procédé de formation d'un film de revêtement multicouche
WO2015147080A1 (fr) * 2014-03-26 2015-10-01 日本ペイント・オートモーティブコーティングス株式会社 Composition aqueuse de revêtement et procédé de formation de film multicouche appliqué en revêtement
JP2016107375A (ja) * 2014-12-05 2016-06-20 株式会社マキタ 電動工具及び動力工具
KR20160129288A (ko) * 2015-04-30 2016-11-09 한국화학연구원 신규한 수용성 공중합체 및 이의 제조방법
KR101705728B1 (ko) * 2015-04-30 2017-02-13 한국화학연구원 신규한 수용성 공중합체 및 이의 제조방법
JP2019014790A (ja) * 2017-07-05 2019-01-31 株式会社Kri 撥水撥油性膜形成用塗布組成物及び撥水撥油性膜

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